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2-Nitro-thioglycosides : α- and β-Selective Generation and Their Potential as β-Selective Glycosyl Donors

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2015

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https://doi.org/10.1021/acs.orglett.5b00295
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Organic Letters. 2015, 17(6), pp. 1421-1424. ISSN 1523-7060. eISSN 1523-7052. Available under: doi: 10.1021/acs.orglett.5b00295

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Michael-type addition of thiolates to 2-nitro-d-glucal or to 2-nitro-d-galactal derivatives readily provides 2-deoxy-2-nitro-1-thioglycosides. Kinetic and thermodynamic reaction control permitted formation of either the α- or preferentially the β-anomers, respectively. Addition of achiral and chiral thiourea derivatives to the reaction mixture increased the reaction rate; the outcome is substrate-controlled. The 2-deoxy-2-nitro-1-thioglycosides are excellent glycosyl donors under arylsulfenyl chloride/silver triflate (ArSCl/AgOTf) activation, and they provide, anchimerically assisted by the nitro group, mostly β-glycosides.

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ISO 690PENG, Peng, Yiqun GENG, Inigo GÖTTKER-SCHNETMANN, Richard R. SCHMIDT, 2015. 2-Nitro-thioglycosides : α- and β-Selective Generation and Their Potential as β-Selective Glycosyl Donors. In: Organic Letters. 2015, 17(6), pp. 1421-1424. ISSN 1523-7060. eISSN 1523-7052. Available under: doi: 10.1021/acs.orglett.5b00295
BibTex
@article{Peng20152Nitr-31382,
  year={2015},
  doi={10.1021/acs.orglett.5b00295},
  title={2-Nitro-thioglycosides : α- and β-Selective Generation and Their Potential as β-Selective Glycosyl Donors},
  number={6},
  volume={17},
  issn={1523-7060},
  journal={Organic Letters},
  pages={1421--1424},
  author={Peng, Peng and Geng, Yiqun and Göttker-Schnetmann, Inigo and Schmidt, Richard R.}
}
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